A chiral acrylate equivalent for metal-free Diels-Alder reactions: endo-2-Acryloylisoborneol

…, JM García, A González, A Lecumberri…

Index: Palomo, Claudio; Oiarbide, Mikel; Garcia, Jesus M.; Gonzalez, Alberto; Lecumberri, Ainara; Linden, Anthony Journal of the American Chemical Society, 2002 , vol. 124, # 35 p. 10288 - 10289

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Citation Number: 28

Abstract

The principle of metal-free activation of enones toward the Diels-Alder reaction with dienes is demonstrated by exploiting the capability of Brønsted acids to activate α'-hydroxyenones through hydrogen bonding. The diastereoselective application of such a principle is nicely realized by using a newly designed family of camphor-based chiral enones, which upon catalytic action of either trifluoroacetic or triflic acid lead to the corresponding cycloadducts ...

 Related Synthetic Route
METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

N/A Structure

465500-08-7

N/A

~0%

(+)-Camphor Structure

464-49-3

(+)-Camphor

1-(4-Methylcyclohex-3-en-1-yl)ethanone Structure

6090-09-1

1-(4-Methylcycl...

N/A Structure

465500-08-7

N/A

~90%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(+)-(1R)-4-methyl-cyclohex-3-enecarboxylic acid Structure

121424-36-0

(+)-(1R)-4-meth...

N/A Structure

465500-02-1

N/A

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

N/A Structure

465500-01-0

N/A

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor


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